Azo-dyestuffs and process of making same



Patented Aug. 16, 1932 UNITED, 5mm

CHEMICAL mnus'rar 11v BASLE, or VBASEL, si'vrrznnnewi5 GERALD BoNHoTfi,"OFVBASUEC'L, SWITZERLAND, ASSIGNOBLTO THE FIRM soornry or lizo-nyusmunrs am) ,r'ieocnss or MAKING SAME an) Drawing. Application filedQctober 24, lsa gseriai no. 570,930, and in Switzerland November 3,13.3.0.

The present invention relates to the manufacture of new azo-dyestufis.It comprises the process of making thesedyestufis, as Well as the newdyestuffs themselves.- n

It has been found thatnew azo-dyestufi's are obtained by 'diazotizing aiiiinoazo-dyestuffs of the general torrnula in which of the five ms twostand for substituents from a group of substituents com prising alkyland alkoxy or for'hydrogen, and the other three stand for hydrogen, andcoupling the diazo-compoundwith an arylide of 2:3-hydroxynaphthoicacidor a derivative thereof, having in the naphthalenenucleus furthersubstituents and capable ofbeing coupled in the 1-position, or with al-hydroxynaphthalene l-ketone.

Among these products those are partlcularly valuable which areobtainedfrom nonsultonatedand non-carbo yla-ted arylides of the 23-hydroxynaphthoicacid, They thus" correspond to the general formulastufis are characterized by their good properties of fastness. When theyare produced on the fibre, Bordeaux red to garnet and violet tints areobtained, which arecharacterized by their good fastnessto-Washing,chlorine and bowking. In this respect sthe dyestufis excel those whichcan be made from aminoazo-dyestuifswhich correspond with the first ofthe above general formulas, with the difference that one or more of thems stand for negative .substituentsr w The following examples illustratethe in vention the partsbeing by weight? I E mampZe 1 i e 22.8 peas ofa'i-amino-ga're hox a eb adyestufi thus formed, which corresponds withthe formula v 7 is immediately precipitated. The garnetred precipitateis filtered, Washed and dried.

I I Example-2 I Cotton yarn is impregnated With a grouiid ing liquor,made by dissolving '5 grains of the wnaphthylaniine. or2z"3-hydroxynap'hthoic acid :in 300 cc. of hot 'Water with additionof101cc. of caustic soda solution of30 per centlstrength and 10 cc. ofTurkey red oil, thevvhole being diluted to Ilitre. The yarn is thenwoundv oil. and developed iiia solution, neutralized-"withsodiumacetate, containing 3 grams of diazotized i-methyl-4E-amino-5-methoXya-z'obenZene perf "litre." There is produced adeepcurrant tint ofexcellent'properties of tastness. The new dyestuficorresponds with the formula I Example v The material which is to beprinted is treated in'the i'Foulard machine with an alkaline solutioncontaining per litre 10 grams of orthoI-anisidide 0132; 3-hydroxynaphthoic' zene arediazotized asusual and the, product; is 'introduced into a solution of 29.3 parts of 2 iBV-hydroxynaphthoicacid-para-anisidide, 60 parts of caustic soda solution offifi percent.strength and,15 part s of calcined so so m Carbonate in 2000 parts ofWater, The

acid. After drying, the material is printed If these dyestufis are to beproduced on wool it is advantageous to work according to the particularsof British Patent No. 310,758. In that patent it has been disclosed thatfor the dyeing of wool with arylides of 2: 3-hydroxynaphthoic acid it isadvantageous" to use such grounding baths which contains per liter0.6'to 1.8 grams of sodium hydroxide. The following table indicates thetints produced on the fibre by some of the dyestufi's of this inventionCoupling component Component diazotized Tint Aryhdes ol 2:3-hydroxynaphthoic acid 4-amino -5- methoxy- Ortho-toluidide Garnetazobenzene Do Para-anisidide Do Do Ortho-anisidide Do DoMeta-nitranilide Currant Do Meta-chloranilide Garnet Do Para-cresidideDo i D0 2: 5-dichloranilide Currant Do I Para-phenetidlde V Garnet Do'Ortho-phenetidide Bordeaux Do 4-chloro-2-toluidide Currant-violet DoB-naphthylamide Garnet Do a-naphthylamide Currant Do rPara-chloranilideGarnet 4 methyl 4' amino Ortho-anisidlde Do 5-methoxyazobenzene DoPara-anisididle Blue-Bordeaux Do 5-ch1oro-2-toluidide Violet Dofl-naphthylamide Garnet Do a-naphthylamide Violet j I)o AnilideB1ue-Bordeaux Do Ortho-phenetidide Bordeaux 4:5 dimethoxy- 4Meta-toluidide Garnet amino-azobenzene Do Ortho-anisidide Currant DoPara-anisidide 7 Do Do 5-chloro-2;toluidide Do Do B-naphthylamide Do Dol a-naphthylamide Garnet Do Anilide Violet 4:5 dlmethoxy- 4-Meta-toluidide Do amlno-azobenzene D0 Meta-toluylene-diamide Currant DoPara-toluidide Violet-garnet Do Ortho-toluidide Violet DoOrtho-anisidide Garnet-violet 4'-amino-5'-methoxyl-hydroxynaphthalene-Garnet azobenzene 4-pheny1ketone What I claim is 1, A manufacture of newazo-dyestuifs by diazotizing an aminoazo-dyestuif of the general formulain whichof the five ws two stand for" submula" stituents from a group ofsubstituents consisting of alkyl and alkoxy or for hydrogen, and theother three stand for hydrogen, and coupling the diazo-compound thusproduced with an arylide of the 2: 3-hydroxynaphthoic acid ofthe'general formula and coupling the diazo-compound thus produced withan arylide of the 2:3-hydroxynaphthoic acid of the general formula n inwhich aryl stands for a non-sulfonated and non-carboxylated nucleus ofthe benzene or naphthalene series.

3. A manufacture ofnew azo-dyestuifs by diazotizing the aminoazodyestuflof the forand coupling the diazo-compound thus produced with an arylideof the 2: 3-hydroxyand noncarboxylated nucleus of the benzene ornaphthalene series. v

i 4, A manufacture of a new azo-dyestuif bydiazotizing theaminoazo-dyestuft' of the formula I and coupling thediazo-compound thusproduced with the arylide of the formula 5. A manufacture of anewazo-dyestuff by diazotizing the aminoazo-dyestuif of the formula andcoupling the diazo-compound thus pro- I duced with the arylide of theformula O-GHa 6. A manufacture of a new az o-dyestuif by diazotizing theaminoazo-dyestufi of the formula O-GHa and coupling the diazo-compoundthus produced with the arylide of the formula 7 As new products theazo-dyestufis of the general formula O-alkyl in which aryl stands for anon-sulfonated and non-carboxylated nucleus of the benzene ornaphthalene series, which products, in a dry state, are dark powders,and which, in case they are produced on the fibre, dye the same fullBordeaux-red to violet tints.

9. As new products the azo-dyestufi's of the general formula in whicharyl stands for a non-sulfonated and non-carboxylated nucleus of thebenzene or naphthalene series, which products, in a dry state, are darkpowders, and which, in case they are produced on the fibre, dye the samefull Bordeaux-red to violet tints.

10. As a new product the azo-dyestufi of I the formula which product, ina dry state, is a dark powder, and which, in case it is produced on thefibre, dyes the same full current tints.

11. As a new product the azo-dyestufi of the formula which product, in adry state, is a dark powder, and which, in case it is produced on thefibre, dyes the same full garnet tints.

12. As a new product the azo-dyestuif of the formula l va- 0 H 0- 113which product, in a dry state, is a dark powder, and which, in case itis produced on the fibre, dyes the same full garnet tints.

In witness whereof I have hereunto signed my name this 17th day ofOctober, 1931.

GERALD BONHOTE.

IOU

